4-Toluenesulfonyl chloride → (5-Methoxy-1,2,3,4-tetrahydro-2-naphthyl)methyl p-toluenesulfonate

HRID 963698Notes

Reaction equation

HRID 963698 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([CH2:13][OH:14])[CH2:8]2.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:14][CH2:13][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[CH:12][C:3]=3[O:2][CH3:1])[CH2:8]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53744579(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 11739484(5-Methoxy-1,2,3,4-tetrahydro-2-naphthyl)methyl p-toluenesulfonateYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)methanol (1.00 g) in dry pyridine (10 ml) was added p-toluenesulfonyl chloride (1.15 g) under ice bath cooling. The mixture was stirred for 1 day at room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with water (twice), 1N hydrochloric acid and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)methyl p-toluenesulfonate (1.70 g) as a white powder. mp: 81°-82° C.

Workup

  1. temperaturecooling
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water (twice), 1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-57704fe45a9341cf8ac6cc0616343903
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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